Membrane-permeant esters of inositol polyphosphates, chemical syntheses and biological applications

Wenhong Li, Carsten Schultz, Juan Llopis, Roger Y. Tsien

Research output: Contribution to journalArticle

60 Scopus citations

Abstract

Membrane-permeant derivatives of inositol polyphosphates are useful tools for biological studies. Racemic 2,3,6-tri-O-butyryl-myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester(Bt3IP3/AM), myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester (IP3/AM), hexakis(propionyloxymethyl) ester (IP3/PM) and hexakis(butyryloxymethyl) ester (IP3/BM) were therefore synthesized. Whereas extracellular application of up to 200 μM of Bt3IP3/AM or IP3/AM to 1321N1 astrocytoma cells failed to mobilize internal calcium, IP3/PM and IP3/BM released internal calcium at concentrations as low os 20 μM and 2 μM, respectively.

Original languageEnglish (US)
Pages (from-to)12017-12040
Number of pages24
JournalTetrahedron
Volume53
Issue number35
DOIs
StatePublished - Sep 1 1997

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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